


Jock's Messy Fall

by shadowcock



Category: Original Work
Genre: Big Cock, Cheating, Crossdressing, Drinking, Drug Use, Gay Sex, Jock - Freeform, M/M, Messy, Mind Manipulation, Pie, Transformation, Whipped Cream, fallen jock, jock bottom, little cock, nerd, nerd revenge, nerd top, pie cream, pie filling
Language: English
Status: Completed
Published: 2018-10-25
Updated: 2018-10-25
Packaged: 2019-08-07 14:09:39
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 5
Words: 7,286
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16409924
Author URL: https://archiveofourown.org/users/shadowcock/pseuds/shadowcock
Summary: Richard Brock was manly and strong until he was slathered in pie filling and whipped cream...





	1. A Pie in the Face is Worth Two in the Crotch

**Author's Note:**

> This is based on a true story... some parts are embellished (the farther in the story you go the more fantasy it becomes) but a lot of it was taken from the real life of "cupcake" (no that's not his real name but) if you want to talk to him he is willing to be anyone's faggot slut... with the right amount of pies lol 
> 
> Tumbler - http://dressmeup-messmeup.tumblr.com/  
> UMD page - https://umd.net/xcup-cakex
> 
> he is looking to find real encounters so if you live in Texas talk to him and maybe you can fuck a crossdressing jock IRL... Oh and be nice and bring a bunch of pies for the slut ;)

Richard Brock was a man’s man... He loved camping he was involved in four different sports and he was athletically built... He was the average jock type; he picked on nerds/dorks/ geeks, he was a star player, he had a lot of girls trying to get at him... But he had grown up he was now a 23yr old office worker and weekend warrior... He even coached a few teams... But only the junior varsity members. Everyone loved him and thought he was the epitome of manliness.

“Come on honey we’re running late,” Cindy said looking for her keys in her bag.

“It’s only a business social.” Richard groaned

“It doesn’t matter, we need to be there because we said we were gonna be there... Do you want to make a lair out of me?” she said half joking. Richard sighed and gave in... 

Richard loved his girlfriend, he felt so lucky having such a fine hot woman next to him... She was smart, elegant, beautiful, slim and curvy in the right areas... and a slutty whore in bed... What more can a man want?

When they arrived at the social they walked around for a bit then suddenly Chris from accounting grabbed him and said “dude, Carver is sick and he said you were his stand in... We need you to cover as the pie throwing target.” 

Chris was an old high school friend... A jock like him, he was in charge of accounting but he barely knew anything about numbers... He was more of a boss type, to answer to the higher-ups and to relay to the drones what the bosses want or expect.

“Crap, I knew he sounded sick yesterday,” Richard said, talking about forcing him to come out and drink with him and the rest of their high school buddies... He would not admit it but he it was his own damn fault he was in this mess... But still, it took his girlfriend to convince him to follow through. 

Soon he was dressed in a thong and a pink crop top...

“What the fuck is this!!!” Richard screamed as if his male pride was being challenged.

“Dude, calm down, it was all we had... That is in your size, it's from the clothing donations a couple stalls down... Things they know would not sell... Plus, Carver has a wetsuit at home with him.” 

Again it took his girlfriend and his jock friends to convince him to go out there dressed like this. They told him the thong was a male thong but he could have sworn it was a female bikini... Still, he had a job to do and he was man enough to follow through... Or at least that was what his girlfriend made him believe.

Soon he was out at the pie throwing stall with goggles and a swimming cap on to protect his hair... And then the pies began... From the first pie he the man felt something in him change the gooey feeling on his skin the creamy mess dripping all over as more pies were thrown at him the more he got turned on, he even loved to squish the pie goop in his hands, the squishy feeling turned him on.

After a couple of hours, Chris waked up to him and told him his shift was done for the day... Richard was a bit disappointed but he didn’t dare let that show. He was hard as fuck but the cream pies filled in the areas where you could tell... The 23yr old man was not that well endowed so his cock was barely average... No one noticed he had a raging hard on the entire time.

The gooey man went to the bathroom to clean up after wiping a good amount of cream off of him a man walked in... It was Arnold Poindexter an ex-schoolmate now an IT tech for the same company... Now from the front with all that cream and goo no one could tell Richard was hard but from the side it was apparent he was turned on. 

“What the fuck are you looking at fag!” Richard said he caught the geek looking at his crotch. With those words, it startled the man and he ran away scared.

Feeling good about scaring the faggy nerd shitless, he cleaned up the rest of the pie mess and changed back into his clothes... He found his girlfriend and enjoyed the rest of the social. 

Even after a few days, Richard was still thinking about how it felt to be covered in that ooey gooey mess... He loved it for some reason... He looked it up and found there were people that just loved getting pies thrown at them they’re called a stooge pie target... Like in the three stooges and their pie fights... Richard focused on that. There was another splosh fetish but he didn’t think he was that type of person... No, he just enjoyed having pies thrown at him. 

About a week later joining a stooge pie target blog, he got an invitation to become a pie target. He really wanted to feel like that again so he took the guy on his offer. 

That weekend he went out... He told his girlfriend he found some camping buddies on and online camping blog and he wanted to hang out with them for a while... She rolled her eyes and gave him that “men” sigh he knows all too well before she told him ok and to be careful.

Richard drove north towards the camping grounds but as soon as he was well away from his home he hooked around and drove to the house where he was to be the pie target. 

It was strange the house was close to his old high school, he didn’t think about it too long and rang the doorbell. A kid answered the door.

“Hey, I’m Franklin, come on in.” the short 5’5” boy said, he was a dork he even wore a pocket protector and had thick black rimmed glasses... All of Richard’s worries faded away... He did not want to admit it but going to a stranger’s house from a blog was a big ass risk but this nerd, he could handle him, he laughed to himself. 

The kid said he was a 19yr old college student studying something... Richard stopped listening a while ago. Then he asked if he wanted to play some video games the jock scoffed and declined, then Franklin asked if he wanted some beer and weed... The jock wholeheartedly agreed to that idea. 

Sometime later after large amounts of beer and weed... The nerd asked if he wanted to start the pie-ing... Richard agreed, he was a little too excited but he was too stoned to care. 

“Ok put this on, unless you brought a change of clothes,” Franklin said, handing him a skimpy leotard.

Richard wanted to complain about this but he was too high to give a fuck... And he was right he did not bring a change of clothes.

“Also you should shave your body hair.” the nerd said handing the jock a very quality razor. 

Richard again wanted to complain but the geek explained to him why it would be better to shave and it made sense... Getting that sticky mess all over, it was hell to get out and most of it stuck on his body hair.

The jock took his time and shaved all over... Well, all the parts he could reach.

“I take it you need help with your back and stuff,” Franklin said taking the razor... Richard just nodded still high as fuck. 

After shaving all of his back the boy asked if he could shave his butt... Richard was too high to even think that was gay he even bent over exposing his ass to the boy as if he were presenting his ass to him...

“Ok shave away,” Richard said not thinking this position was gay at all.

The 19yr old lathered up some shaving cream... Richard was surprised it was warm to the touch, it was his body temperature so all he felt was the creamy smoothness covering his muscular ass. The boys deceptively strong hands lathered the shaving cream all over the jock’s ass... the squishy soapy feeling reminded Richard about the messy pies from before making his cock twitch a little... The kid shaved his ass, once in a while he felt a finger graze his ass hole and it made the jock quiver a little... 

“Ok turn around,” he told the jock, “and hold on to these.” the boy made him hold onto his knees making the jock spread his ass wide open like a fucking faggot slut but again Richard didn’t put two and two together he still thought this was totally innocent. 

Franklin began to shave the man’s balls taking into his hands an carefully shaving the delicate skin... Even if he was not thinking this was gay Richard thought this was hot and his cock was leaking precum like it was a tiny fountain... This did embarrass the jock though making his face glow red. 

“Done!” he said shaving the last bit of hair... 

Richard stood up and even though he was already naked he felt more naked than he ever felt before... He had not an inch of hair on his body and it made him feel weak somehow but he could not understand it.

The jock then put on the leotard and told him he was ready... But instead of throwing the pie the boy stuck a finger into the pie and licked it off then slowly finger fucked the pie and wiped it on the jock’s face... Then he slathered more pie onto the man. The pie was room temperature so there was no cold shock he just felt the gooey feeling again. The messy creaminess getting worked into his muscular chest as the goo slowly made its way down into his crotch and crack of his ass... This was the feeling he craved he loved it.

After all that squishy goodness Richard noticed that the pies were already almost all gone... When Franklin walked up with the last pie and slowly smushed it into his face the goop slowly moved down like slimy fingers gently massaging his body... Then the boy wiped the pie cream from his face and stuffed those gooey fingers into the jock’s mouth... Richard wanted to get mad but his mind was too wasted.

“You fucking pie whore” Richard suddenly heard he wasn’t even sure where it was coming from... That nerd would never call this masculine alpha male a whore or any other name.

“Fucking Dick head, are you listing?” he felt a sharp slap upside his head... the words were reaching Richard but he could not imagine being talked down to by such a skinny nerd so it took a while to understand what was going on.

“Come on pie fag!” The kids said.

Richard finally accepted he was being talked down to by the college nerd... His instincts were to punch the disrespectful runt in the face... But being covered in this mess, dressed in a leotard and he was a little sure he came a little when he heard the words “pie fag” made him more subservient... Instead of getting mad, the jock’s face became red hot from being humiliated to the point of cumming. 

“Look you fucking loser you even came from being talked down to.” the boy laughed and this made Richard even harder. Then the kid grabbed the cream around his cock and brought it to his mouth.

“Eat it you fucking baby dicked bitch!” the boy said with a wicked look in his eyes. Richard tried to fight it but his mouth slowly opened and licked the cummy cream... It was the first time he had ever tasted cum but the sweetness from the pie and the salty pungent taste from the cum made the man savor his own jizz. The jock was too busy thinking about the flavor that he didn’t hear the laughter from the boy as he watched this once strong jock eating cum flavored cream like it was ambrosia.

After that, they both went upstairs where changed Franklin changed back to his normal nerdy self and offered his a shower so he can go home clean and that is what Richard did.

When he got home it was late, his wife was in bed and the jock was only left with the memories of what just happened. The man looked up the splosh kink and saw this was what he was into but he was also into humiliation apparently... So he spent a few hours jacking off to names he wanted Franklin to call him... He came three times imagining being talked down to by the nerd.

The next day

Before he left for a date with his girlfriend Richard checked his email... He noticed one message that had “pie fag” as the subject line... His cock got instantly hard. it read:

To my sissy pie fag,

I know you enjoyed our fun pie time, maybe next time we can take it farther, I know you are a sissy bitch just waiting to get out... If this scares you, I understand that you are too chicken to explore this side of yourself... I just want to see how much a pie whore you are. 

Sincerely,  
Your Nerd Master 

Again he felt rage bubbling up and he wanted to drive down to that faggot nerd’s house and beat the crap out of him... But his cock was twitching in anticipation on what his new master would make him do next week. 

to be continued in the next chapter


	2. Lube... Just Desserts

**Summary for the Chapter:**

> Richard Brock is still a big man with his girlfriend... but with Franklin...

The week went by in a flash and soon Richard was ready to lie to his girlfriend again... and again his lame lie worked, this time it had to do with fishing.

Richard found himself back in front of the door of that nerd boy... He rang the doorbell and Franklin opened the door again welcoming him in as if they were new friends. He was acting so normal that he thought last week was all a bad dream. That was until they went downstairs. 

“Here put this on.” the boy said handing him girly clothes that were perfectly his size.

“Fuck NO!!” Richard said still eyeing those clothes.

“Really? What a shame I guess you came down here for no reason.” Franklin said nonchalantly, and the kid headed upstairs.

“WAIT!…” Richard said as if he were desperate but also swallowing that word. “F-fine...” he said grabbing the clothes from the guy's hands.

After he put the clothes on he felt more ashamed then he had ever felt before and his dick was harder then it had ever been... He was so hard his cock actually ached. He looked like a total slut... He was wearing hot pink long thigh high net stocking, a neon yellow tiny girly bikini bottom, he wore a red bra that was stuffed with silicone mounds making the jock look like he had proper boobs, and a white tied crop-top that made his red bra show clearly through... Everything was brought together with a perfectly fitting blond wig. He looked at himself and it made him mad... So mad... Fucking enraged... That is all looked so well on him, he looked like the skankiest whore he had ever seen. He would have paid good money to fuck a girl like him. 

“Good now let's get started, whore,” Franklin said with his wicked smile again.

Again they started with the pies the goo got everywhere... Dressed like this there were more places the slimy cream could get into. This time Franklin was more hands-on, he covered the sissy jock with pie after pie, rubbing it into his skin, shoving his gooey hands into the cracks and crevices of the whore jock... He pushed his hands into Richard’s muscly ass, rubbing the man’s anal ring.

“You are such a whore pushing your ass back like that,” Franklin said pushing the man’s hole but not enough to enter. Then he moved up to the jock’s fake titties he groped them and massaged them as the boy licked the chocolate cream off of the feminine jock’s back.

“I-I don’t know why... Oooohhhh...” Richard trailed off

“You don’t know what?” Franklin said feigning ignorance... He knew what the jock was going to say.

“I-I d-don’t know w-why t-this makes m-me s-so h-h-horny.” the jock said as if spitting out nasty tasting words.

“It’s because you are a sissy faggot inside,” Franklin said squeezing the jock’s muscular butt again, “I bet you feel sexy when I grope your girly ass, don’t you?” he said as he aggressively groped his ass all the way to his balls the creamy goo acted like lube making it easier for the boy so rub the sissy jock’s ass and balls. 

All Richard could do was moan in agreement... Then the man felt something big and hard between his legs. it surprised the fuck out of Richard.. The pie cream acted like lube so it was easy for Franklin to push his cock between the jock’s legs. He felt the thick monster rub push open his thighs closest to his crotch and he felt the hard meat stick push past his balls.

“W-what the fuck is that!?” Richard said, not being able to process what was happening... 

“I guess you’ve never seen a cock have you?” Franklin said laughing as he grabbed Richard’s hard 5 inches.

It was his cock? Richard thought how could a cock be THAT big? It was 10 inches at least and as thick as his own wrist. This was it he was broken the sissy turned around and matched up his cock with the boy’s cock... It was like comparing a baby carrot to a two-liter bottle of coke... It wasn’t even close any sense of male pride he had left was shattered while he held that heavy meat stick. Richard fell to his knees in defeat... Thinking back he finally realized why he called him a baby dicked bitch...

Franklin took this opportunity and grabbed a pie... Boston cream, he began to fuck it in front of the sissy jock’s face and then cream covered he pulled it out and grabbed the man’s hair making him open his mouth... Breaking his mind it was easy to slide his thick cock into the pie fag’s mouth, as he pushed in the extra cream was left on Richard’s face and he face fucked him pushing cream everywhere.

“Look at your faggot pie hole... So mess, but that is what a faggots mouth is for isn’t it?” Richard was so far gone that he just nodded, “That’s right fucking baby dicked faggot. You dork ass cock gobbler... Faggot ass dick grazer...” and the boy continued to call Richard all kinds of names as he fucked his mouth. “I bet you didn’t know your mouth was a pussy too.” Franklin laughed at him as he used his mouth just like a pussy. 

All Richard could do was relax his throat and take the massive cock as it came... Luckily he looked up how to give a blowjob for a week now... He was hoping, deep inside to be used like this but he didn’t know how huge his cock was going to be but it was true his mouth was starting to feel like a pussy as the guy pushed deeper and deeper into his mouth... Then the boy moaned screaming “take it bitch!” and shot after shot of hot thick creamy cum blasted the back of his throat and his face over and over again. He didn’t mean to but Richard unconsciously licked up the cream that was shot onto his face... 

“Wow, I didn’t even have to ask you to clean that up.” Franklin laughed... The laughter cemented the embarrassment the jock felt as he realizes what he was doing.

He could not believe he was brought down so hard. He was brought down a peg- no more than a peg... He was a certified cock sucking sissy... A cum hungry, faggot loser, desperate to lick up cum sprayed onto his face like he was a cheap whore. How could he ever let himself fall so low... But... He wanted more... 

Franklin grabbed him by the hair and lowered his head and said, “I bet you're excited about what I have planned for my baby dicked faggot next week.” Richard looked deep in his master’s eyes, licked more cum and nodded his head. 

to be continued in the next chapter


	3. Pie Hole Discovery

**Summary for the Chapter:**

> Richard Brock always thought he was a man... a manly man... but he soon discovers his new pie hole.

Richard was living his life like he always had... He was dominate with his girlfriend in bed, he joked with the boys at work, he teased nerds at work and whenever he had the chance to... But he is hiding a secret... He is an insatiable little bimboi slut to a big cocked nerd master and he loved every minute of it. 

This week dragged on though he looked forward to the emails he was getting from his master calling all sorts of humiliating names and telling him if he was ready to take the next step. The man was not stupid he knew he was gonna get fucked and fucked hard but with such a big cock he had to get his sissy ass ready for the fucking. 

On the first day, he was instructed on how to clean his ass properly and then he was taught how to finger his ass... He had to do it after he used the bathroom at home... He needed to clean properly and finger... By the time the day was over he was able to finger fuck his ass with four fingers and vaseline... On the second day, he was instructed to finger his ass but then later in the day he would have to use a cucumber... So he bought one and put a condom on it... There were none the size of his master but he got a good sized one. He played with his ass all week long this way.

The day came and he went to his master’s house... He walked in and Franklin was trying to do his get comfortable thing before they went downstairs but Richard asked to go down.

“Wow, I didn’t know you were in such a rush to be a whore.” Franklin laughed. Richard just looked embarrassed for being so impatient... 

Soon Richard was dressed in a black net top and matching net stockings, he also wore pink thong panties, a plaid miniskirt this time he had worn a pink wig with braided pigtails and to finish it up he wore hot pink lipstick and makeup... Richard looked up how to do make up all week so he could look like a proper whore for his master... He made sure it was everything proof... The only way to ruin this makeup was to use a special solvent that came with it. So he would ensure he would look like a damn good sissy streetwalker all night. He looked like a whore dressed as a Catholic school girl.

“Ok, is your ass clean?” Franklin asked

“Yes sir, I cleaned it deep before I left,” Richard answered as if to a superior.

“Have you done your sissy anal exercises?” Franklin asked as if he were reading off a list.

“Yes sir, I can fit all five fingers now but not my whole hand... Sorry, sir I tried.” Richard said a bit defeated. 

“Ok get in position.” the boy said, watching the compliant sissy get on all fours. 

Then the pies were brought out... But this time there was pudding, whipped cream, and whipped topping in a can... “We are gonna have fun tonight,” Franklin said grabbing a hand full of pudding and dripping it down the back of the sissy jock.

Soon they were all covered in messy gooey cream and dessert... This is when Franklin grabbed a hand full of fresh whipped cream and the boy began to push his fingers into it... The cream made it easy to stick his finger to slide in and out (the practice didn’t hurt either) but the boy could tell his ass was still tight, this was good. The boy pushed more fingers into the man’s ass. The more the bitch moaned the deeper Franklin wanted to go. The boy alternated with whipped cream, pudding and the pie cream all over the place. He was milking the sissy and it was working, Richard was moaning like a bitch as he pushed his ass back, trying to get the fucking hand deeper into his hole. Then when he knew he was gonna cum Franklin held onto the jock’s sissy clit making sure to saturate his thong panties with as much cum as he could. 

“Oh fuck yes! Yes!! Make me cum from my ass!!!!” Richard screamed in his new sissy girly voice. When he was done cumming Franklin took off the sissy’s panties and stuffed it into his mouth. 

“This is for being such a good girl,” Franklin said as he stuffed Richard’s faggot mouth with his own cummy panties. Then he pushed the faggot’s head down and raised his ass... This made the bitch wag his tail in anticipation. 

Before he started the boy took the canned whipped cream and wrote pie slut onto his muscular ass then took the can and sprayed as much cream into the sissy ass as he could. Then he took vanilla pudding and slathered it onto his massive cock and slowly entered the sissy hole. 

Richard could feel it... The sheer size of the head made his own head reel as he felt it pushed its way past his anal ring... The jock sissy learned a lot while fucking his own ass all week and he began to use everything he learned, like pushing out as the massive cock pushed in, it made it easier for the object to push through... He was a faggot savant... Using every trick to take his master’s cock. 

“That’s it pie slut, take my cock.” Franklin said as he drove his huge cock deeper. “come on baby back bitch take my fucking rod!” he was getting deeper and deeper... As if calling him names made it easier to get deeper into his ass “that's if butt boi faggot... Only a little more.” he said, Franklin's balls were almost touching Richard’s balls... After a few more deep thrusts he was finally balls deep. Franklin slapped Richard’s ass hard making the bitch moan. “Finally!” the boy said after waiting for the slut to get used to his massive cock being that deep... He began to plow the sissy deep and hard. 

With his thong still hanging from his mouth, now sucked clean, Richard began to speak, “Oh yes!!! Fuck my sissy jock ass, fuck my hole I love cock so much!!!” he screamed letting his inner slutty bimboi out... They fucked in all positions and finally when Richard was on his back getting pounded hard by his nerdy master... All the creamy gooey pie and pudding surrounding them... Richard’s legs widespread in the air like a common whore... The sissy jock came for the third time that day... but this time onto his own face... This made Franklin cum hard into the sissy’s pussy.

“There now you have a proper pussy... Aren’t you glad sissy whore?” Franklin said leaving he softening cock in the jock’s newly minted pussy. 

“Oh thank you, sir, for giving me such a wonderful pussy!!!” Richard was actually tearing up. He was not sure if it was because his pride as a man was completely dead... For the rest of his life, he will NEED to be fucked like a cheap whore... Even if he stays with his girlfriend... Or if he was so happy that he finally knows that his ass was always a pussy... He just needed the right cock to prove it to him... This is what he pondered as cum filled his pussy and tears rolled down the broken alpha’s cheek. 

to be continued in the next chapter


	4. Sweet, Sweet Revenge of the Nerds

**Summary for the Chapter:**

> His master has set up a party for Richard to go to... who's party and why do the cars look so familiar?

It had been about half a year since Richard first met Franklin... The jock had learned how to balance his life... As before he is still an alpha to his girlfriend and “the man” at work. Not much has changed... Except for every weekend he would go to his nerd master’s house and become a sissy bimboi covered in cake pie cream and other gooey things. 

The beginning of this week Richard was sent an email stating their meeting spot would change and that his pussy and mouth pussy would be shared at a party. The meeting place was deeper in the city and a little closer to where he lives... But this did not worry him he knew his master was smart and there as no way he would get caught and he was excited to be used by others.

-weekend-

“Honey are you sure you can’t come? I hear many of your coworkers will be there.” Cindy whined

“Sorry babe but this week there is a “secret meeting” and I was told I had to be there... I think they said someone would be “inducted” into the group... They are very hush-hush about these things.” Richard said now used to lying to his girlfriend. 

“Ok, but I think you’re missing out,” she said as she kissed him goodbye. “I am going, so don’t be jealous when you see me on Jim’s arm,” she said teasingly.

After that Richard left to the new meeting place... There was a birthday going on and the whole hall looked filled to the brim... Many of the cars seemed familiar. He was told to enter in from the back where he meets with his master? When he walked in, there was a lot of commotion going on. 

“Come here.” said what looked like an organizer. Richard saw his master smiling and with a nod, he knew he was to follow these people’s orders to a tee.

Richard was sat in a chair and a makeup artist began to clean his face prepping it for a full transformation... After a while the man could not recognize his face in the mirror, then his hair was made to fit in a head sock, so a wig could be fastened onto his head it was blond and flowing... Curly and it made Richard feel kinda dumb and bubbly. 

“Done! Wardrobe!!!” screamed the makeup artist and Richard was zipped to another area with pink clothes. 

“hummmm...” said a female fashion designer.

She pondered for a moment... Then she got to work faster then Richard could even process... He was sure he changed at least a dozen times and the man didn’t even notice when they put the realistic fake boobs on him... But when he looked into the mirror he thought he was looking at a high-class bimbo whore. He had on white thigh high stockings with pink frilly tops, he had on long knee high fuck-me boots with pink laces going up the side with hidden padding in the knees (this was why his master taught him how to walk in 9in fuck-me boots a while back, Richard thought), he also had on white garters with pink frills, a soft pink corset with wight frills, white gloves with pink patterns and a frilly pink top, a collar (or choker) that read cupcake, and a frilly soft pink skirt with pink and white lace rosettes... It was low enough that it hid his tiny raging hardon and balls, they were tied close to his body and clad in a silky pink thong.

Then Richard was led out onto the hall... With other bimbo women... About ten others from what Richard could tell they were real women but he also looked like a real woman so he was not sure, all he knew was they were all whores and he was part of them. Franklin had whispered “your name is cupcake...” before he was pushed out into the crowd.

Richard was surprised there were a lot of familiar faces in the crowd he saw Chris from accounting, Jim from finance, Dan from downstairs... This was the party Cindy was talking about! Richard thought he was freaking out... But he knew if he looked worried he would be caught so he clammed down and put on the high-end whore bimbo persona he was supposed to be. So walked out there with confidence and his girliest voice he could do. It was working too... 

It was strange he was getting talked up by his coworkers... Chris groped him a few times... Actually, he was groped by all of his high school buddies at least twice lucky his balls and cock were bound tight so they did not feel anything else but his butt and the way he was tied up made it feel like he had an outline of a pussy... This was strange, he was flirting with his former school buds and current coworkers. Many of them offered to fuck him but as his master told him that his pussy was reserved and he could only do anal... So he was brought to the bathroom plenty of times... Taking load after load in his pussy by his coworkers... Some of them took pics. 

He even saw some old nerdy class mates at the party and he was told not to refuse any cock in the party so many of the geeks, dorks, and nerds he bullied... The strange thing is that each and every one of those guys took a picture with him and all called him “cupcake” as if they knew it was not her name or that they knew who he really was... This made Richard even hornier and humiliated but he could not prove it. Though being fucked... used by the fat and totally lanky nerds he used to bully made him feel so... So... Horny... It did not help that he could not get off cause his penis was tied too tightly nothing could cum out so he got no satisfaction... 

Then the festivities stopped when the lights went out and spotlights were aimed at a man sitting on a large throne-like chair... It was Arnold Poindexter...

“Ok folks its time to honor the man of the hour my brother Arnold!!!” Franklin said coming out of the dark next to his brother. 

Oh fuck, thought Richard... The man thought about all the fucked up shit he put Arnold and his friends though if HE exposed him here it would be VERY bad, Richard thought.

“Ok everyone knows we have... “escorts” with us tonight and the winner of the escort popularity contest will “wish” my brother a very happy birthday.” Franklin said as the crowd joined in on an all-knowing laugh. “and the winner is.…” there was a drum roll during his pause, “CUPCAKE!!!” he screamed out.

Richard was now being led to Arnold his heart jumped when he spotted Cindy, she is standing next to Jim... She smiles at Richard... Oh, shit does she know? He wonders but outside he just smiled back at her. Then Franklin reached out his hand and took him and lead him to Arnold... But not before whispering “he will keep your secret.” to Richard’s relief. 

“Ok everyone, back to the party!!” Franklin said as the lights came back on and Arnold and Richard were led into another room.

-in another room-

“I can’t believe that’s you, Richard,” Arnold said laughing at the man, “oh, sorry I mean Cupcake.” the nerd let out another humiliating laugh. Richard’s face got bright red... It even showed past all that makeup. 

“You know I was the one that told my brother about you and that got him to turn you onto the bimbo whore you are now... I saw your pathetic tiny hardon that day... You got turned on by pie filling.” he laughed again... He was getting undressed...

“Oh fuck!!” Richard screamed in his girly voice when he saw Arnold’s cock it was 12 inches fully hard and thicker than his brother’s... The sissy’s knees went wobbly and his mouth just fell open, whether it was from shock or getting his sissy mouth ready to be used... Even the sissy jock didn’t know. 

Arnold slowly pushed his cock into the dressed up jock whore’s mouth... The man struggled a bit but quickly got used to the thick invader. 

“You are going to be my personal plaything, my brother will use you when I'm not using you... And you will report to the house at least twice a month... More if we call you.” Arnold said... Richard could only nod his head he was too lost in feeling this huge cock in his mouth, Arnold knew he would have to explain this later. 

Then Arnold pulled his cock out of the jock’s mouth and slapped him with the thick monstrosity... His own saliva and some pre-cum splattered onto the man’s face. Richard knew he should hate this but it only turned the sissy whore on even more. Arnold walked behind the sissy slut and slapped the jock’s ass when he reached it... 

“Do you remember all those times you stuffed me into my own locker?” Arnold slapped the athletic man’s buns... All Richard could do was moan a weak “uh huh” in response, “all those time you beat me or one of my friends up?” again he answered “uh huh” “well this is where we pay you back for all of that torture...” Arnold was right behind Richard he reached over and grabbed him by the face and said, “but a slutty whore like you will love this wouldn’t you?” 

Richard wanted to say “no” but he couldn’t, he knew deep down, he loved being paraded around then fucked like he was today... He loved the attention he got but most of all... He was anticipating how this large meat pol that was wedged between his cheeks would feel shoved deep into his sissy hole... Fuck, he wanted it so badly he was afraid he would start begging any moment now. 

Without a word, Arnold grabbed a large piece of his cake and slathered all of it onto the shaft... He then slowly pushed his arm-like cock deep into his, now well trained, pussy... “oooooooohhhhh fuck...” the man said as he felt the sweet sticky cake frosting and crumbs pile up against his ass... 

This was when Franklin lifted up the man whore’s face and shoved his cake covered cock down his throat... This cock felt so familiar... It calmed Richard down a little like a long and thick pacifier... He knew how to work this dick... The two brothers fucked the jock’s holes over and over... Switching places and reminding him how much of a loser jock he was forgetting used by two geeks and nerds... 

The night went on and the party heard the sissy jock moaning and beg for cock as the night went on... But to them, they just thought it was the sexy cupcake being fucked by the nerdy Arnold... And every time the crowd heard a moan they cheered “CUPCAKE!!!” …they did it a lot that night. 

By the night’s end, the sissy jock and ex-bully was on the floor covered in cake, with a well-used pussy leaking frosting and cum.

-The next day- 

Richard came home (he cleaned himself off at Franklin’s shower)… His girlfriend met him in the hallway dressed in the same type of dress he was wearing at the party... 

“Hey baby...” she said in her sexiest voice, “I want your meat stick baby!” Richard realized she was impersonating HIM from the party. He was not sure if she knew nor did he know if she was fucking with his mind dressing like this.

“Ohhhh... Baby, you should have been at the office party, you know, for that nerd in IT...” she said “There was this gorgeous whore- I mean escort.” she giggles trying to push up her tits to look bigger... Richard was still holding his breath not sure what to make of this... “you should have seen her she was fucking hot.” she laughed “If you were there I would have let you play with her pussy... But only if I could play too.” she said winking at him... Richard finally exhaled realizing she had no idea that he was Cupcake. 

To be concluded in the next chapter


	5. Epilouge - Cupcake as a cow-girl

**Summary for the Chapter:**

> Richard is going to the comicon...

Even months after the party many people were still talking about Cupcake and how hot she was... Most of his bros kept showing him pictures of them cream-pieing the whore’s hole... Cindy had forgotten about her but still puts the dress on once in a while to feel sexy.

Not much had changed for Richard except he had a secret meeting on the weekends with his strange camping group. It was not so often that Cindy would get worried but it was enough to notice. 

This weekend was going to be long because he was going to a comic con with Arnold, Franklin and their friends... 

He was not sure what he was doing walking around dressed as a cow-girl in pigtails (not a girl version of a cowboy but a girl that was dressed like a big titted cow)... He wore fake breast harnesses that made him look like he was an F-cup he had gel-like hip padding that made him look like he had even more sexy curves and he wore a corset that shaped him into a feminine shape... He looked at himself and his tiny cocklet barely made a tent. His costume was your normal slutty cow-girl... He wore a white corset with large black spots on them... Like a cow motif... He wore black thigh high stockings, white legwarmers with large black spots... He even wore cow style high heels... This insured the jock would walk sexy, he wore elbow length gloves that matched the cow style they were going for and a choker with a cowbell and finally he wore soft cow horns to complete the look. 

The nerds paraded him around many men grabbed and groped him, making the jock feel even more humiliated... Finally, when the first day was over Arnold his brother and his gang of nerds and geeks went to his room. 

They sat him in the middle and they all pulled out their cocks... He was instructed to “moo” only and if he did not he was slapped in the face with a fat cock. 

Many of the nerds fondled his breast but the smart ones began to fuck his holes... His mouth and his sissy pussy... They used custard as lube that night and the sissy jock was filled with custard from mouth to pussy... And the next day he was put out in the hallway dressed as power girl... His legs were tied up in the air and hands bound, exposing his sissy clit and pussy... And he was told to keep his mouth opened all day... There was also a note that read “I am a cum dump whore that needs a lot of geek and nerd cum...” there was a tub of frosting next to him for lube... 

The man cursed his masters for “forcing” him to do this but he could not deny he was so turned on that he loved every nerd and geek that used his holes that day... 

The End

**Author's Note:**

> Just in case you missed it this cross-dressing princess slut wants attention so contact him through his tumblr and UMD page... 
> 
> Tumbler - http://dressmeup-messmeup.tumblr.com/  
> UMD page - https://umd.net/xcup-cakex
> 
> and if you want to fuck him IRL... you have to be in texes or close and talk to him to set it up... oh and fuck the roses get him a dozen pies hahah...


End file.
